Three Perfect Days in Islamorada

Just 90 minutes south of Miami, Islamorada is the ‘key’ to a perfect getaway! The Florida Keys are made up of 1,700 islands, though only 42 are connected by bridges; six of which comprise the village of Islamorada.

STAY

The Post Card Inn Beach Resort & Marina at Holiday Isle is an oceanfront oasis ideal for both relaxation and recreation. Each of the boathouse-chic guest rooms has the signature island-style of white woods, sand-colored stripes and nautical décor. It’s a comfy and convenient choice with on-site restaurants, water sports and beach access.

Image credit: Post Card Inn Beach Resort & Marina at Holiday Isle

The resort also arranges snorkeling, sunset cruises, various eco-tours, swimming with dolphins, tiki jet flying, and party boat excursions.

PLAY

Nighttime Paddle boarding. Image credit: Aquaholic Adventures

After check-in, head straight to the Post Card’s world-famous Tiki Bar, home of the first-ever rum runner! Cheers to island-time with this fancy umbrella drink while overlooking the spectacular blue and green Atlantic waves.

Ready to dive into fun? Pick your adventure: jet ski, kayak, paddle boarding and kite boarding rentals and lessons are all available with hourly rates so you to choose just how ambitious you want to be. Nighttime stand up paddle boarding (SUP) will allow you to see the Keys in a new light. Aquaholic Adventures night tours use LED-lit paddle boards and kayaks with the added luminescence of shooting stars, full moons and vibrant fish.

Islamorada is best known as the “Sport fishing Capital of the World.” Captain Rick Rodriguez, owner of Seahorse Charters, is an expert fisherman specializing in the catch of sailfish and mahi-mahi. Head to Whale Harbor Marina to board his 39-ft., 3-tiered boat for the most exciting half-day or full-day charter experience. You may catch blue marlin, wahoo, tuna, amber jacks, queen snappers, triple tail and more.

The sunshine state has two lobster seasons: a two-day mini recreational season in July (before commercial traps are placed) and an 8-month recreational & commercial season (August-March). Drive down A1A to Bud N’ Mary’s Fishing Marina, established in 1944 and now home to over 40 offshore captains and backcountry guides, to meet up with Captain Sara Stanczyk for lobster hunting! She’s mastered the sport of locating Florida Spiny lobsters in rocks, crevasses and coral heads. Lobstering is challenging but you’ll savor the fun and sweet, delicate flavor of these crustaceans.

Bass Pro Shops. Image credit: Debbie Lacy

Back on land, discover native wildlife with a hike at Indian Key State Historic Site & Park, Windley Key Fossil Reef Geological State Park or Lignumvitae Key Botanical State Park. Or rent bikes to geocache along the island with a pit stop at Bass Pro Shops. Inside this water-sport wonderland, explore Hemingway’s magnificent boat. Then, head out back to the dockside restaurant to sip yumminess beside swarming tarpon.

DINE

Head to Lorelei Restaurant & Cabana Bar for the best sunset entertainment, because tunes from a tiki stage just sound better! Nosh on peppercorn-crusted tuna, Keys conch chowder and Lorelei’s famous frozen key lime pie.

Claiming to have the “best bunz in town,” opt for a sweet breakfast at Bobs Bunz. Choose from savory muffins, cookies, pies and, of course, delicious cinnamon bunz and sticky buns.

Image credit: Wahoo’s Bar and Grill

Recharge at Wahoo’s Bar & Grill, situated above the marina with bartenders sending down homemade drinks on a rope and wood caddy! This breathtaking oceanfront spot might just be the best on the whole island. Eat tropical scallops, oysters on the half shell and fresh Mahi-mahi sandwiches.

If you do any fishing during your visit, take your fresh catch to Lazy Days Restaurant, where the chef will prepare the fish and lobster that you caught! Or, feast on Keys-style dishes at an oceanfront table on the outdoor patio with a menu comprised of local seafood, pastas, huge sandwiches and certified Angus steaks.